Peroxisome proliferator-activated receptor γ-dependent activity of indole ring-substituted 1,1-bis(3'-indolyl)-1-(p-biphenyl)methanes in cancer cells

Cancer Chemotherapy and Pharmacology

Volumn 66, Issue 1, 2010, Pages 141-150

  Guo, Jingjing ^a   Chintharlapalli, Sudhakar ^a   Lee, Syng Ook ^a   Cho, Sung Dae ^b   Lei, Ping ^a   Papineni, Sabitha ^c   Safe, Stephen ^a,c  

^a TEXAS A AND M HEALTH SCIENCE CENTER   (United States)

^b Institute Wonkwang Biomaterial Implant   (South Korea)

^c TEXAS A AND M UNIVERSITY   (United States)

Author keywords

C DIMs; Indole ring substituents; PPAR agonists

Indexed keywords

1,1 BIS(3' INDOLYL) 1 (PARA BIPHENYL)METHANE DERIVATIVE; CAVEOLIN 1; KRUPPEL LIKE FACTOR 4; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; PROTEIN P21; UNCLASSIFIED DRUG; 1,1 BIS(3' INDOLYL) 1 (4 BIPHENYL)METHANE; 1,1-BIS(3'-INDOLYL)-1-(4-BIPHENYL)METHANE; CDKN1A PROTEIN, HUMAN; CYCLIN DEPENDENT KINASE INHIBITOR 1A; INDOLE DERIVATIVE; KRUPPEL LIKE FACTOR; NUCLEAR RECEPTOR NUR77;

ARTICLE; CANCER CELL; CANCER INHIBITION; COLON CANCER; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG MECHANISM; DRUG STRUCTURE; HUMAN; HUMAN CELL; NORTHERN BLOTTING; PANCREAS CANCER; PRIORITY JOURNAL; PROTEIN INDUCTION; RECEPTOR UPREGULATION; STRUCTURE ACTIVITY RELATION; TRANSACTIVATION; WESTERN BLOTTING; CELL PROLIFERATION; CHEMISTRY; COLON TUMOR; DRUG EFFECT; DRUG POTENTIATION; DRUG SCREENING; GENETIC TRANSFECTION; METABOLISM; PANCREAS TUMOR; SYNTHESIS; TUMOR CELL LINE;

CAVEOLIN 1; CELL LINE, TUMOR; CELL PROLIFERATION; COLONIC NEOPLASMS; CYCLIN-DEPENDENT KINASE INHIBITOR P21; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDOLES; KRUPPEL-LIKE TRANSCRIPTION FACTORS; NUCLEAR RECEPTOR SUBFAMILY 4, GROUP A, MEMBER 1; PANCREATIC NEOPLASMS; PPAR GAMMA; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSFECTION;

EID: 77951896704     PISSN: 03445704     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00280-009-1144-0     Document Type: Article

References (29)

1. Hong J, Samudio I, Liu S, Abdelrahim M, Safe S (2004) Peroxisome proliferator-activated receptor γ-dependent activation of p21 in Panc-28 pancreatic cancer cells involves Sp1 and Sp4 proteins. Endocrinology 145:5774-5785
2. Vanderlaag K, Su Y, Frankel AE, Grage H, Smith R III, Khan S, Safe S (2008) 1, 1-Bis (3'-indolyl)-1-(p-substituted phenyl) methanes inhibit proliferation of estrogen receptor-negative breast cancer cells by activation of multiple pathways. Breast Cancer Res Treat 109:273-283
3. Chintharlapalli S, Smith R III, Samudio I, Zhang W, Safe S (2004) 1, 1-Bis (3'-indolyl)-1-(p-substitutedphenyl) methanes induce peroxisome proliferator-activated receptor γ-mediated growth inhibition, transactivation and differentiation markers in colon cancer cells. Cancer Res 64:5994-6001
4. Chintharlapalli S, Papineni S, Baek SJ, Liu S, Safe S (2005) 1, 1-Bis (3'-indolyl)-1-(p-substitutedphenyl) methanes are peroxisome proliferator-activated receptor gamma agonists but decrease HCT-116 colon cancer cell survival through receptor-independent activation of early growth response-1 and NAG-1. Mol Pharmacol 68:1782-1792
5. Chintharlapalli S, Papineni S, Safe S (2006) 1, 1-Bis (3'-indolyl)-1-(p-substituted phenyl) methanes inhibit colon cancer cell and tumor growth through PPARγ-dependent and PPARγ-independent pathways. Mol Cancer Ther 5:1362-1370
6. Chintharlapalli S, Papineni S, Safe SH (2007) 1, 1-Bis (3'-indolyl) - 1-(p-substitutedphenyl) methanes inhibit growth, induce apoptosis, and decrease the androgen receptor in LNCaP prostate cancer cells through PPARγ-independent pathways. Mol Pharmacol 71:558-569
7. Contractor R, Samudio I, Estrov Z, Harris D, McCubrey JA, Safe S, Andreeff M, Konopleva M (2005) A novel ring-substituted diindolylmethane 1, 1-bis[3'-(5-methoxyindolyl)]-1-(p-t-butylphenyl) methane inhibits ERK activation and induces apoptosis in acute myeloid leukemia. Cancer Res 65:2890-2898
8. Qin C, Morrow D, Stewart J, Spencer K, Porter W, Smith R III, Phillips T, Abdelrahim M, Samudio I, Safe S (2004) A new class of peroxisome proliferator-activated receptor γ (PPARγ) agonists that inhibit growth of breast cancer cells: 1, 1-bis (3'-indolyl)-1-(psubstitutedphenyl) methanes. Mol Cancer Therap 3:247-259
9. Vanderlaag K, Samudio I, Burghardt R, Barhoumi R, Safe S (2005) Inhibition of breast cancer cell growth and induction of cell death by 1, 1-bis (3'-indolyl) methane (DIM) and 5, 5'-dibromo-DIM. Cancer Lett 236:198-212
10. York M, Abdelrahim M, Chintharlapalli S, Lucero SD, Safe S (2007) 1, 1-Bis (3'-indolyl)-1-(p-substitutedphenyl) methanes induce apoptosis and inhibit renal cell carcinoma growth. Clin Cancer Res 13:6743-6752
11. Abdelrahim M, Newman K, Vanderlaag K, Samudio I, Safe S (2006) 3, 3'-Diindolylmethane (DIM) and derivatives induce apoptosis in pancreatic cancer cells through endoplasmic reticulum stress-dependent upregulation of DR5. Carcinogenesis 27:717-728
12. Calabro P, Samudio I, Safe SH, Willerson JT, Yeh ET (2005) Inhibition of tumor necrosis factor-α-induced endothelial cell activation by a new class of PPARγ agonists: an in vitro study. J Vascular Res 42:509-516
13. Kassouf W, Chintharlapalli S, Abdelrahim M, Nelkin G, Safe S, Kamat AM (2006) Inhibition of bladder tumor growth by 1, 1-bis (3'-indolyl)-1-(p- substitutedphenyl) methanes: a new class of peroxisome proliferator-activated receptor γ agonists. Cancer Res 66:412-418
14. Lei P, Abdelrahim M, Safe S (2006) 1, 1-Bis (3'-indolyl)-1-(psubstituted phenyl) methanes inhibit ovarian cancer cell growth through peroxisome proliferator-activated receptor-dependent and independent pathways. Mol Cancer Ther 5:2324-2336
15. Cho SD, Yoon K, Chintharlapalli S, Abdelrahim M, Pei P, Hamilton S, Khan S, Ramaiah SK, Safe S (2007) Nur77 agonists induce proapoptotic genes and responses in colon cancer cells through nuclear receptor-dependent and independent pathways. Cancer Res 67:674-683
16. Chintharlapalli S, Papineni S, Jutooru I, McAlees A, Safe S (2007) Structure-dependent activity of glycyrrhetinic acid derivatives as peroxisome proliferator-activated receptor γ (PPARγ) agonists in colon cancer cells. Mol Cancer Therap 6:1588-1598
17. Chen ZY, Tseng CC (2005) 15-Deoxy-Δ12, 14 prostaglandin J2 up-regulates Krüppel-like factor 4 expression independently of peroxisome proliferator-activated receptor γ by activating the mitogen-activated protein kinase kinase/extracellular signal-regulated kinase signal transduction pathway in HT-29 colon cancer cells. Mol Pharmacol 68:1203-1213
18. Escher P, Wahli W (2000) Peroxisome proliferator-activated receptors: insight into multiple cellular functions. Mutat Res 448:121-138
19. Fajas L, Debril MB, Auwerx J (2001) Peroxisome proliferatoractivated receptor-γ: from adipogenesis to carcinogenesis. J Mol Endocrinol 27:1-9
20. Suh N, Wang Y, Honda T, Gribble GW, Dmitrovsky E, Hickey WF, Maue RA, Place AE, Porter DM, Spinella MJ, Williams CR, Wu G, Dannenberg AJ, Flanders KC, Letterio JJ, Mangelsdorf DJ, Nathan CF, Nguyen L, Porter WW, Ren RF, Roberts AB, Roche NS, Subbaramaiah K, Sporn MB (1999) A novel synthetic oleanane triterpenoid, 2-cyano-3, 12-dioxoolean-1, 9-dien-28-oic acid, with potent differentiating, antiproliferative, and anti-inflammatory activity. Cancer Res 59:336-341
21. Rieusset J, Touri F, Michalik L, Escher P, Desvergne B, Niesor E, Wahli W (2002) A new selective peroxisome proliferatoractivated receptor y antagonist with antiobesity and antidiabetic activity. Mol Endocrinol 16:2628-2644
22. Berger JP, Petro AE, Macnaul KL, Kelly LJ, Zhang BB, Richards K, Elbrecht A, Johnson BA, Zhou G, Doebber TW, Biswas C, Parikh M, Sharma N, Tanen MR, Thompson GM, Ventre J, Adams AD, Mosley R, Surwit RS, Moller DE (2003) Distinct properties and advantages of a novel peroxisome proliferator-activated protein γ selective modulator. Mol Endocrinol 17:662-676
23. Koyama H, Miller DJ, Boueres JK, Desai RC, Jones AB, Berger JP, Macnaul KL, Kelly LJ, Doebber TW, Wu MS, Zhou G, Wang PR, Ippolito MC, Chao YS, Agrawal AK, Franklin R, Heck JV, Wright SD, Moller DE, Sahoo SP (2004) (2R)-2-ethylchromane-2-carboxylic acids: discovery of novel PPARα/γ dual agonists as antihyperglycemic and hypolipidemic agents. J Med Chem 47:3255-3263
24. Acton JJ III, Black RM, Jones AB, Moller DE, Colwell L, Doebber TW, Macnaul KL, Berger J, Wood HB (2005) Benzoyl 2-methyl indoles as selective PPARγ modulators. Bioorg Med Chem Lett 15:357-362
25. Liu K, Black RM, Acton JJ III, Mosley R, Debenham S, Abola R, Yang M, Tschirret-Guth R, Colwell L, Liu C, Wu M, Wang CF, Macnaul KL, McCann ME, Moller DE, Berger JP, Meinke PT, Jones AB, Wood HB (2005) Selective PPARγ modulators with improved pharmacological profiles. Bioorg Med Chem Lett 15:2437-2440
26. Schopfer FJ, Lin Y, Baker PR, Cui T, Garcia-Barrio M, Zhang J, Chen K, Chen YE, Freeman BA (2005) Nitrolinoleic acid: an endogenous peroxisome proliferator-activated receptor γ ligand. Proc Natl Acad Sci USA 102:2340-2345
27. Baek SJ, Wilson LC, Hsi LC, Eling TE (2003) Troglitazone, a peroxisome proliferator-activated receptor γ (PPARγ) ligand, selectively induces the early growth response-1 gene independently of PPARγ. A novel mechanism for its anti-tumorigenic activity. J Biol Chem 278:5845-5853
28. Baek SJ, Kim JS, Nixon JB, DiAugustine RP, Eling TE (2004) Expression of NAG-1, a transforming growth factor-β superfamily member, by troglitazone requires the early growth response gene EGR-1. J Biol Chem 279:6883-6892
29. Chintharlapalli S, Papineni S, Liu S, Jutooru I, Chadalapaka G, Cho SD, Murthy R, You YJ, Safe S (2007) 2-Cyano-lup-1-en-3-oxo-20-oic acid, a cyano derivative of betulinic acid, activates peroxisome proliferator-activated receptor γ in colon and pancreatic cancer cells. Carcinogenesis 28:2337-2346 (Pubitemid 350111592)